EP0342517A2 - Procédé d'impression par rongeage et rongeage-réserve avec usage de réductones aminées - Google Patents

Procédé d'impression par rongeage et rongeage-réserve avec usage de réductones aminées Download PDF

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Publication number
EP0342517A2
EP0342517A2 EP89108465A EP89108465A EP0342517A2 EP 0342517 A2 EP0342517 A2 EP 0342517A2 EP 89108465 A EP89108465 A EP 89108465A EP 89108465 A EP89108465 A EP 89108465A EP 0342517 A2 EP0342517 A2 EP 0342517A2
Authority
EP
European Patent Office
Prior art keywords
printing
amino
atoms
radical
etching
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP89108465A
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German (de)
English (en)
Other versions
EP0342517A3 (fr
Inventor
Peter Dr. Lechtken
Peter Kutschera
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP0342517A2 publication Critical patent/EP0342517A2/fr
Publication of EP0342517A3 publication Critical patent/EP0342517A3/fr
Withdrawn legal-status Critical Current

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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/15Locally discharging the dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642Compounds containing nitrogen
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92Synthetic fiber dyeing
    • Y10S8/921Cellulose ester or ether
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92Synthetic fiber dyeing
    • Y10S8/922Polyester fiber
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92Synthetic fiber dyeing
    • Y10S8/924Polyamide fiber

Definitions

  • the present invention relates to a process for printing polyester, cellulose acetate, cellulose triacetate or polyamide and their mixtures containing textile materials with etchable or etchable disperse dyes according to the etching pressure or etching reserve printing process, in which an aqueous etching printing or etching reserve printing paste containing an amino reductone as an etchant, an aqueous Contains solution of a thickener and optionally an etch or etch reserve-resistant dispersion dye, is pattern-printed on the textile material and the textile material printed in this way is then fixed and washed out.
  • Etching printing is a process in which the dyes already on the textile material are partially or completely destroyed by chemicals.
  • Classic etching printing is based on real, finished dyeings on which an etching paste is printed.
  • the etchable background dyes are destroyed in the printed areas and white etching results.
  • the etching paste also contains etch-resistant dyes, the so-called illumination or colored dyes, a colored set is created.
  • a variant of classic etching printing is the etching reserve printing, in which the dyes to be destroyed sit on the fiber surface but are not yet fixed.
  • etching agents which contain, for example, a strongly alkaline compound or a reducing agent, such as tin-II salts, in particular tin-II-chloride, or derivatives of methanesulfinic acid , where alkali-cleavable or reducible dyes for the basic dyeing of the fiber materials to be printed are destroyed as completely as possible by the etchant, while alkali-resistant or irreducible dyes as illuminating dyes for colored effects (in contrast to white effects in the absence of illuminating dyes) to achieve patterns of any size with as much as possible not sharp contours on the fiber materials to be printed by the etchant be destroyed.
  • a strongly alkaline compound or a reducing agent such as tin-II salts, in particular tin-II-chloride, or derivatives of methanesulfinic acid
  • alkali-cleavable or reducible dyes for the basic dyeing of the fiber materials to be printed are destroyed as completely as
  • the etching agents used in the known methods can have the following disadvantages: - severe fiber damage due to alkali - Corrosion on printing presses, particularly on dampers, through the formation of HCl - Heavy metal pollution of the wastewater when using, for example, tin salts - Exhaust air and wastewater contaminated with formaldehyde when using methanesulfinic salts.
  • the object of the present invention is to provide a new etchant in which the disadvantages mentioned above are avoided as far as possible.
  • -Atoms can be substituted in the alkyl radical or acetoxy groups, or a radical - (CH2-CH2-O) n H, in which n represents the numbers 1 to 10 and which is etherified with an alkyl radical with 1 to 3 carbon atoms or with a Acetyl may be esterified, stands or R4 forms together with the N atom the residue of an aliphatic ⁇ - or ⁇ -amino acid having 2 to 15 carbon atoms, the carboxyl group present being neutralized as an alkali, alkaline earth or ammonium salt or esterified in the form of a C1 to C10 alkyl ester, or their mineral acid salts as etchants for etching printing and etching reserve printing processes, the disadvantages mentioned above can be avoided.
  • the invention provides new, advantageous etching agents.
  • the 3-amino reductones of formula I and their mineral acid salts are outstandingly suitable for their strong reducing power reductive removal of reducible disperse dyes on textile materials containing polyester, acetate, triacetate or polyamide and their mixtures.
  • the compounds of the formula I can be in the form of mineral acid addition salts due to the amino group. Hydrochlorides, sulfates and hydrogen sulfates are particularly suitable.
  • alkyl radicals for R4 having 1 to 20 C atoms are n-hexyl, n-octyl, 2-ethylhexyl, 3,5,5-trimethylhexyl, n-decyl or n-dodecyl, the radicals having 8 to 14 C atoms are preferred.
  • Alkenyl radicals are, for example, octenyl or decenyl.
  • the alkyl or alkenyl radicals can have 1 to 3 OH groups as substituents, which can be etherified, for example, by methyl, ethyl or propyl or esterified by acetyl.
  • substituents can be etherified, for example, by methyl, ethyl or propyl or esterified by acetyl.
  • residues of R4 containing alkoxy groups are ethoxyethyl, polyethoxyethyl, ethoxypropyl, diethoxypropyl, 2-acetoxyethoxyethyl and similar residues obtained by reaction of ethylene oxide or propylene oxide.
  • aliphatic ⁇ - or ⁇ -amino acids formed from the rest R4 together with the N atom, may be mentioned, for example, glycine, ⁇ -alanine, ⁇ -alanine, valine, leucine or isoleucine, phenylglycine or ⁇ -aminocaproic acid.
  • Particularly preferred amino reductones of formula I and their acid addition salts are those in which R1, R2 and R3 represent a hydrogen atom and R4 together with the N atom is derived from glycine, ⁇ -alanine, ⁇ -alanine or ⁇ -aminocaproic acid and where the carboxyl group is optionally present as the sodium, potassium, calcium or ammonium salt.
  • 3-amino reductones of the formula I are known compounds, for example they are described in European Patents 83 008 or 124 752. This prior art shows that they are suitable for stabilizing organic compounds or organic compositions against oxidative influences and that amino reductones can influence the growth of animals. It was by no means obvious and it was all the more surprising to find that such amino reductones can be used as advantageous etching agents under the conditions of the etching pressure or etching reserve printing process.
  • amino reductones of the formula I can be prepared, for example, exactly analogously to the processes described in European Patents 83 008 and 124 752, so that further explanations are not necessary.
  • lactones can be formed, in particular with an ⁇ -amino acid, which can then be used for their invention Use to be saponified in the usual way.
  • the present invention relates to a process for printing on textile materials made of polyester, cellulose triacetate, acetate and polyamide and their mixtures with one another using disperse dyes according to the etching printing or etching reserve printing process, characterized in that a 3 -Aminoreductone of the general formula I or whose acid addition salt is used with the meanings defined and preferred above, and the use of an amino reductone of the formula I or its acid addition salt as an etchant for disperse dyes by the etching pressure or etching reserve printing process.
  • the particular advantages of the amino reductones to be used in the printing pastes are the low application rate, the ease of degradation and the avoidance of heavy metals and stabilizers.
  • the development of formaldehyde when printing on the textile materials is avoided with the printing pastes according to the invention.
  • the amino reductones of the formula I are used in a manner known per se and known to the person skilled in the art in the form of printing pastes for the etching printing or etching reserve printing together with thickeners and, if appropriate, etching-resistant disperse dyes and the customary auxiliaries.
  • These printing pastes contain, based on the weight, 1 to 10% by weight, preferably 5 to 7% by weight, of an amino reductone of the formula I or its acid addition salt.
  • the textile goods are printed, e.g. Woven or knitted fabrics made of polyester, cellulose acetate, cellulose triacetate or polyamide or mixtures thereof. Textiles from the types of fibers mentioned are known. Disperse dyes are used almost exclusively as dyes.
  • the etching reserve printing process can be carried out, for example, by first padding the textile material with a liquor which contains an etchable disperse dye.
  • the textile material can also be printed with a printing paste which contains an etchable disperse dye together with a thickener.
  • the textile material is then dried under conditions such that the dyes are not yet fixed.
  • the textile is then printed with a mixture of an etch-resistant disperse dye and the etchant according to the invention and dried.
  • the dyes are then fixed, e.g. by thermosolating or heating the textile goods in a superheated steam atmosphere. Under these conditions, the etchable dye is destroyed at the locations on which the mixture of the etch-resistant dye and the etchant has been printed. This procedure is called the etching reserve because the base of the goods is colored, but the dye is not yet fixed.
  • a variant of the etching reserve method is that the mixture of etch-resistant dye and reducing agent is printed on the textile and immediately afterwards the etchable dye is overprinted over the entire surface and the material is then dried and the dyes are fixed.
  • an etchable dye that has already been fixed on the tissue is etched with the etchant mixture according to the pattern.
  • White etching is also possible in all process variants, ie in this case a printing paste is used which contains an etchant mixture but no dye.
  • the dyeing of polyester can be carried out using carriers as well as under high temperature conditions, e.g. Dyeing under pressure in an aqueous liquor at 120 ° C.
  • the reductive post-cleaning required for polyesters takes place after printing and fixing, i.e. The rear and the areas printed for illumination are reductively cleaned in one work step.
  • the advantage of the coloring is the better levelness of the background, which is particularly important if, due to the pattern, only a few small areas are to be etched.
  • Pre-dyeing gives qualitative advantages, especially for knitted fabrics and very light fabrics. Synthetic fibers made of acetate or polyamide or their mixtures are dyed at a temperature of 85 ° C.
  • disperse dyes are used almost exclusively for the process according to the invention. Suitable dyes of this type can be found in the Color Index.
  • Etchable disperse dyes are those that are decomposed by the etchant into products that generally should not interfere with the white background or the colorful illumination. These are primarily disperse dyes that are derived from azo dyes.
  • the etch-resistant dyes are mainly disperse dyes based on anthraquinone derivatives. They are resistant to the etchant.
  • the printing paste with which the etchant according to the invention is printed on the textile material generally contains a thickener to adjust the viscosity.
  • a thickener to adjust the viscosity.
  • natural thickening agents such as meal flour ether, e.g. Carob flour or starch ether thickeners, such as guar ether, etherified cellulose or starch, and alginates.
  • 1000 parts of the finished printing paste contain 20 to 100 parts by weight of a natural thickener.
  • synthetic thickeners are, for example, high molecular weight polycarboxylic acids, e.g. Polyacrylic acid and copolymers of ethylene and acrylic acid or copolymers of styrene and maleic anhydride, the carboxyl groups of which can be partially or completely neutralized.
  • Etch-resistant disperse dyes can be found, for example, in the color index. Some etch-resistant disperse dyes may be mentioned as examples: yellow disperse dye CI 58 900 and CI 47 023, orange disperse dye CI 60 700, red disperse dye CI 60 755, CI 62 015 and CI 60 756, violet disperse dye CI 61 105, blue disperse dye CI 61 500, CI 62 500 and CI 63 285.
  • 1000 parts by weight of the printing paste contain 0.5 to 50 parts by weight of a disperse dye or a mixture of disperse dyes.
  • the printing pastes which contain the etchant, thickener and etch-resistant disperse dyes according to the invention, can further contain the auxiliaries known per se to the person skilled in the art, such as, based on the total weight, for example 3 to 5% by weight urea or thiourea, 0.1 to 0.3 %
  • auxiliaries such as polyethylene glycol, phenylglycine, dicarboxylic acids or anthraquinone-2-sulfonic acid.
  • the rest of 100% by weight consists of water.
  • a printing paste for etching printing or etching reserve printing 1 to 10% by weight, preferably 5 to 7% by weight, of an amino reductone of the formula I or its acid addition salt, 2 to 10% by weight, preferably 6 to 7% by weight, of a natural or synthetic thickener, optionally 0.5 to 5% by weight of etch-resistant disperse dye, 3.0 to 5.0% by weight of urea or thiourea, 0.1 to 0.3% by weight of foam damper, 8 to 12% by weight of fixative and up to 100% by weight of water.
  • Suitable etchable disperse dyes can also be found in the color index. These are essentially azo dyes. Examples include the yellow disperse dye CI 11 855 and the red disperse dye CI 11 150 and CI 11 115.
  • the parts given in the examples are parts by weight. The percentages relate to the weight of the fabrics.
  • residue A The following is the rest referred to as residue A.
  • the production of the aminoreductones is carried out under nitrogen.
  • a solution of 150 g (2 mol) of glycine and 450 ml of water is mixed with 106.5 g (0.83 mol) of A-OH and 75 ml of 2-normal hydrochloric acid and heated to boiling. At about 40 ° C, a clear solution is formed, from which the process product begins to precipitate at about 80 ° C. After the boiling temperature has been reached, the mixture is cooled to 10 ° C. and the precipitate, a yellowish crystal powder, is worked up as usual. Recrystallization from hot isopropanol gives the amino reductone in 88% yield in the form of colorless crystals, mp. 185 to 187 ° C.
  • a polyester fabric is dyed in an aqueous liquor with the following dye composition at 120 ° C in the HT apparatus: 8.5% Disperse Blue CI 106 0.7% Disperse Yellow CI 5 0.3% Disperse Red CI 224 1.8% Disperse Red CI 118 0.6% Disperse Blue CI 149
  • the tissue is then rinsed and at max. 100 ° C dried. A black color is obtained.
  • a pattern ink of the following composition is printed on the goods dyed in this way: 600 g Guar ether thickening of pH 7 (120 g guar ether in 1000 g water) 100 g a mixture of polyethylene glycol (molecular weight approx. 300) and phenylglycine (approx. 2: 1) 50 g Aminoreductone 4 40 g of the blue disperse dye Disperse Blue CI 56 210 g water 1000 g
  • the printed material is dried and then steamed for 15 minutes with superheated steam at 175 ° C at normal pressure.
  • a blend of 65% 2 1/2 acetate and 35% polyamide is mixed with 5% Disperse Blue C.I. 106 dyed, rinsed and dried at 80 ° C.
  • a dark blue color is obtained.
  • the dye is fixed.
  • the goods colored in this way are printed with the following printing ink: 600 g Guar ether thickening of pH 7 (120 g guar ether in 100 g water) 100 g a mixture of polyethylene glycol (mol. weight 300) and phenylglycine (about 2: 1) 50 g of a dicarboxylic acid mixture 50 g Thiourea 50 g Anthraquinone-2-sulfonic acid 50 g Aminoreductone 4 40 g of the red disperse dye Disperse Red CI 11 60 g water 1000 g
  • the printed goods are dried and then steamed for 20 minutes with saturated steam at 102 ° C at normal pressure.
  • a polyester fabric is padded with a liquor that contains the following components 60 g / l Disperse Blue CI 148 25 g / l Disperse Red CI 118 5 g / l Disperse Yellow CI 198 10 g / l a copolymer of acrylic acid and acrylamide, partially neutralized with sodium hydroxide solution, 5 - 10 g / l the sodium salt of nitrobenzenesulfonic acid
  • the pH value of the padding liquor is adjusted to pH 5.5 with monosodium phosphate.
  • the fleet intake is 60 to 70%.
  • the fabric After padding, the fabric is dried at temperatures in the range of 90 to 100 ° C. The dyes are not fixed. Then the fabric is printed with a printing ink of the following composition: 600 g Guar ether thickening pH 7 (120 g guar ether in 1000 g water) 100 g a mixture of polyethylene glycol molecular weight 300 and phenylglycine) 50 g Aminoreductone 4 40 g of the red disperse dye Disperse Red CI 352 210 g water
  • the printed material is dried and then steamed for 15 minutes with superheated steam at 175 ° C at normal pressure. It is then rinsed cold and reductively cleaned as usual.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP19890108465 1988-05-19 1989-05-11 Procédé d'impression par rongeage et rongeage-réserve avec usage de réductones aminées Withdrawn EP0342517A3 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3816999 1988-05-19
DE3816999A DE3816999A1 (de) 1988-05-19 1988-05-19 Aetzdruck- und aetzreservedruckverfahren unter verwendung von aminoreduktonen

Publications (2)

Publication Number Publication Date
EP0342517A2 true EP0342517A2 (fr) 1989-11-23
EP0342517A3 EP0342517A3 (fr) 1991-11-13

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP19890108465 Withdrawn EP0342517A3 (fr) 1988-05-19 1989-05-11 Procédé d'impression par rongeage et rongeage-réserve avec usage de réductones aminées

Country Status (4)

Country Link
US (1) US4929249A (fr)
EP (1) EP0342517A3 (fr)
JP (1) JPH0219582A (fr)
DE (1) DE3816999A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2164824A1 (fr) * 1971-12-24 1973-08-03 Basf Ag
DE2744607B1 (de) * 1977-10-04 1979-03-29 Basf Ag Verfahren zum Nachbehandeln von gefaerbten oder bedruckten Synthesefasern
JPS57210085A (en) * 1981-06-19 1982-12-23 Mitsui Toatsu Chemicals Printing of synthetic fiber material
EP0083008A2 (fr) * 1981-12-28 1983-07-06 BASF Aktiengesellschaft Aminoréducteurs et matières organiques stabilisées par des aminoréducteurs comme antioxydants
EP0124752A1 (fr) * 1983-04-07 1984-11-14 BASF Aktiengesellschaft Mélanges de matières favorables à la croissance et à l'augmentation de rendement ainsi que fourrage et liquides d'abreuvage contenant des petites quantités de ces mélanges

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2164824A1 (fr) * 1971-12-24 1973-08-03 Basf Ag
DE2744607B1 (de) * 1977-10-04 1979-03-29 Basf Ag Verfahren zum Nachbehandeln von gefaerbten oder bedruckten Synthesefasern
JPS57210085A (en) * 1981-06-19 1982-12-23 Mitsui Toatsu Chemicals Printing of synthetic fiber material
EP0083008A2 (fr) * 1981-12-28 1983-07-06 BASF Aktiengesellschaft Aminoréducteurs et matières organiques stabilisées par des aminoréducteurs comme antioxydants
EP0124752A1 (fr) * 1983-04-07 1984-11-14 BASF Aktiengesellschaft Mélanges de matières favorables à la croissance et à l'augmentation de rendement ainsi que fourrage et liquides d'abreuvage contenant des petites quantités de ces mélanges

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPIL, Nr. 83-13368K, Derwent Publications Ltd, London, GB; & JP-A-57 210 085 (MITSUI TOATSU CHEM. INC.) 23-12-1982 *

Also Published As

Publication number Publication date
JPH0219582A (ja) 1990-01-23
EP0342517A3 (fr) 1991-11-13
DE3816999A1 (de) 1989-11-30
US4929249A (en) 1990-05-29

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